B-lactam compounds
AssigneeSumitomo Pharmaceuticals Company, Limited
InventorMakoto Sunagawa
Life of this patent
Estimating the term…
Abstract
Novel .beta.-lactam compounds belonging to carbapenem or penem derivatives useful as antimicrobial agents or intermediates therefor and a process for producing these compounds are disclosed.
Claims38
A .beta.-lactam compound represented by the formula:
- ##STR427## wherein R.sub.1 represents a 1-hydroxyethyl group or a 1-hydroxyethyl group in which the hydroxy group is protected with a protecting group for a hydroxy group;
- R.sub.2 represents a hydrogen atom or a protecting group for an amino group;
- R.sub.3 represents a hydrogen atom or a protecting group for a carboxyl group;
- X represents an unsubstituted methylene group and Y represents a group of the formula (2):
- ##STR428## wherein R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, an aralkyl group having 1 to 3 carbon atoms in the alkyl moiety thereof, a substituted alkyl group having 1 to 4 carbon atoms wherein said substituent is selected from the group consisting of hydroxyl, di-(C.sub.1 -C.sub.3)-alkylamino or carbamoyl, or R.sub.5 and R.sub.6 are taken together to represent an alkylene chain or an alkylene chain via an oxygen atom, a sulfur atom or a (C.sub.1 -C.sub.3)alkyl-substituted nitrogen atom to form, together with the adjacent nitrogen atom, a 4- to 7-membered cyclic amino group, and a pharmaceutically acceptable salt thereof.
A .beta.-lactam compound represented by the formula:
- ##STR429## wherein R.sub.1 represents a 1-hydroxyethyl group or a 1-hydroxyethyl group in which the hydroxy group is protected with a protecting group for a hydroxy group;
- R.sub.2 represents a hydrogen atom or a protecting group for an amino group;
- R.sub.3 represents a hydrogen atom or a protecting group for a carboxyl group;
- X represents a substituted methylene group of the formula (1):
- ##STR430## wherein R.sub.4 represents an alkyl group having 1 to 3 carbon atoms;
- and Y represents a group of the formula (2):
- ##STR431## wherein R.sub.5 and R.sub.6, which may be the same or different, each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aralkyl group having 1 to 3 carbon atoms in the alkyl moiety thereof, a substituted alkyl group having 1 to 4 carbon atoms wherein said substituent is selected from the group consisting of hydroxyl, di-(C.sub.1 -C.sub.3)-alkylamino or carbamoyl, or R.sub.5 and R.sub.6 are taken together to represent an alkylene chain or an alkylene chain via an oxygen atom, a sulfur atom or a (C.sub.1 -C.sub.3)-alkyl-substituted nitrogen atom to form, together with the adjacent nitrogen atom, a 4- to 7-membered cyclic amino group, and a pharmaceutically acceptable salt thereof.
A .beta.-lactam compound of the formula:
- ##STR433## wherein Y is chosen from the group consisting of ##STR434## and the pharmaceutically acceptable salts thereof.
A .beta.-lactam compound of the formula:
- ##STR435## wherein Y is selected from the group consisting of ##STR436##
(5R)-3-[2-((1-Pyrrolidino)carbonyl)pyr rolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2- carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5R)-3-[2-((1-Azetidino)carbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl )-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5R)-3-[2-((2-Hydroxyethyl)methylamino carbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-3- ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5R)-3-[2- (1-Morpholinocarbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[ 3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5R)-3-[2-(1-N-Methyl piperazinocarbonyl)pyrrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2 ,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2-Carbamoylpy rrolidin-4-ylthio]-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2 -carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2-(Dimethylaminocarbonyl)pyrrolidin-4-ylthio]-4-methyl-6-(1-hyd roxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2-((1-pyrrolidino)carbonyl)pyrrolidin-4- ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-c arboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2-((1-Azatidino)carbonyl)pyrrolidin-4-ylthio]-4-methyl-6-(1-hyd roxyethyl)-1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2-((2-Hydroxyethyl)methylaminocarbonyl)p yrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept-2-e ne-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)- 3-[2-(1-Morpholinocarbonyl)pyrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl) -1-azabicyclo[3,2,0]hept-2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2-(1-N-Methylpiperazinocarbony l)pyrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2,0]hept- 2-ene-7-one-2-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
(5S)-3-[2- Carbamoylpyrrolidin-4-ylthio]-4-methyl-6-(1-hydroxyethyl)-1-azabicyclo[3,2, 0]hept-2-ene-7-one-carboxylic acid, or a non-toxic pharmaceutically acceptable salt thereof.
A .beta.-lactam compound of the formula:
- ##STR441## and the pharmaceutically acceptable salts thereof.
A .beta.-lactam compound of the formula:
- ##STR442## and the pharmaceutically acceptable salts thereof.
A .beta.-lactam compound of the formula:
- ##STR443## wherein Y is chosen from the group consisting of ##STR444## and the pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.